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Water → 3-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

HRID 2407331
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2407331
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:2]1.C(=O)(O)[O-].[Na+].[CH2:19]([O:26][C:27]1[C:36]2[O:35][CH2:34][C@H:33]([CH2:37]OS(C)(=O)=O)[O:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([O:26][C:27]1[C:36]2[O:35][CH2:34][C@H:33]([CH2:37][N:1]3[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]4[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=4)[CH2:2]3)[O:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 12937952Phenol, 3-(3R)-3-piperidinyl-HCID 86644728Methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Produkt 1

HCID 684875373-[(R*)-1-((S)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenolAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of hydrochloride salt of (R*)-3-(piperidin-3-yl)-phenol (240 mg, 1.12 mmol) and sodium bicarbonate in N,N-dimethylformamide (3 ml) were stirred at +120° C. under nitrogen atmosphere. To this mixture, a mixture of methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (390 mg, 1.11 mmol) in N,N-dimethylformamide (3 ml) was added, and stirred at +130° C. for 3.5 h. The reaction mixture was cooled down, water (20 ml) and ethyl acetate (15 ml) were added and the layers were separated. Organic phase was recovered and water layer was extracted twice with ethyl acetate. Organic phase and ethyl acetate extracts were combined and washed five times with water and saturated sodium chloride solution. The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified with flash chromatography using heptane and ethyl acetate as eluents to give 160 mg of the title compound.

Aufarbeitung

  1. additionwas added
  2. stirringstirred at +130° C. for 3.5 h
  3. temperatureThe reaction mixture was cooled down
  4. customthe layers were separated
  5. customOrganic phase was recovered
  6. extractionwater layer was extracted twice with ethyl acetate
  7. washwashed five times with water and saturated sodium chloride solution
  8. dry with materialThe combined organic phase was dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe crude product was purified with flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7997b99eff2a4b7c9a2f3c1370b173a7
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809536B2

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